Press SPACEBAR to Continue on the Modern-Day Oregon Trail

Are you a proud 90s child? Do you occasionally sport a t-shirt that reads “You have died of dysentery”? Kindred spirits, it’s time to head West to check out what’s going on in some of the territories that defined the iconic Oregon Trail computer game! Press DOWN ARROW to continue.

Meet Us in Saint Louis (Before You Get Cholera)

In keeping with the game’s storyline, we begin our westward journey in Saint Louis, Missouri. Be sure to enjoy some premier bubbly beverages at at Saint Louis’ famous Crown Candy Kitchen, which boasts the city’s oldest soda fountain. Delight in the flavors of a Johnny Rabbit Special Malt, a drink comprised of fresh bananas with whipped cream, nuts, and nutmeg. Next, catch a classic feature at the Hi-Pointe Theatre (est. 1922). This theater serves beer and wine to its adult costumers and screens old-timey features on a nightly basis. Do refrain from informing your server that you’re travelling West by way of the Oregon Trail, and make sure not to drink and horse-and-buggy about town. Be responsible and book a night at the luxurious Chase Park Plaza, located in the heart of town on a road lined by mansions and old, beautiful trees. Wake up, admire the streets in the morning light, and hit the trail!

Rest Up at Independence Rock, Wyoming

Though its summit is only 136 feet above the terrain that surrounds it, wind-faceted Independence Rock, located 50 miles southwest of Casper, Wyoming on Highway 220, sits 6,028 feet above sea level and is one of the most notable sites on the Oregon Trail. Pioneers used to carve their names into the rock, which fittingly earned the nickname “The Register of the Desert.” There’s no camping allowed at Independence Rock, but it’s only a five hour drive to Salt Lake City, Utah, so cross-country travelers can stop and rest to increase health and morale of the “wagon” crew.

Feel Young and Alive in Utah Territory (Where the Hunt is Good and the Beer is Plentiful)

After fording a few rivers, hunting buffalo like a regular William Frederick Cody, and perhaps even losing a few close friends to exhaustion along the way, you’re almost there! You’ve made it to Salt Lake City! Visit the awe-inspiring Natural History Museum of Utah (admission, $13; hours, 10 a.m. to 5 p.m.) and check out the Native Voices Exhibit, which explores the traditions and important histories of Utah’s five native nations: Shoshone, Goshute, Paiute, Ute, and Navajo. From the museum, move to The Garage, where trailblazing enthusiasts delight in the mouth-watering taste of juicy burgers and animated beers, and where they dance all night to Salt Lake City’s best bands. Let your wagon air out for the night and sleep in the fine cotton sheets of The Grand America Hotel.

“Congratulations! You have made it to [Portland], Oregon! Let’s see how many points you have received”

Let’s be honest: Hipmunk travellers are the winningest travellers, especially on the Oregon Trail. What better place to spontaneously break into a shameless victory dance than in Portland? Take a celebratory walk on the lush green trails of The Forest Park Conservancy, and marvel at the surreal beauty of the eastern slopes of the Tualatin Mountains. Alternatively, cool off with a cold brew at the Portland Brewing Company Taproom, which offers customers twelve different varieties of beers on draft. It’s perhaps worth noting that, on September 19th, the brewery will be hosting a Scottish Festival from 1 p.m. to 5 p.m., featuring live Scottish music (bagpipes!) and dancing to ‘celebrate the return of Noble Scot Scottish ale’! More adventurous trekkers should pay a visit to Voodoo Doughnuts in Portland’s Old Town. Local favorites include the Memphis Mafia doughnut, the Captain My Captain doughnut, and the legendary Bacon Maple Bar doughnut. Those who frequent this shop occasionally bear witness to legal wedding events; where better to ring in an eternity of love, devotion, and mutual, charmed manipulation than at a voodoo-inspired doughnut shop?